CA2262868C - Bridged metallocene complex for the (co)polymerization of olefins - Google Patents
Bridged metallocene complex for the (co)polymerization of olefins Download PDFInfo
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- CA2262868C CA2262868C CA002262868A CA2262868A CA2262868C CA 2262868 C CA2262868 C CA 2262868C CA 002262868 A CA002262868 A CA 002262868A CA 2262868 A CA2262868 A CA 2262868A CA 2262868 C CA2262868 C CA 2262868C
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 61
- 150000001336 alkenes Chemical class 0.000 title abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 64
- 239000005977 Ethylene Substances 0.000 claims abstract description 42
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 32
- 239000002184 metal Substances 0.000 claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 23
- 230000003197 catalytic effect Effects 0.000 claims abstract description 23
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 22
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000000129 anionic group Chemical group 0.000 claims abstract description 11
- 239000010936 titanium Substances 0.000 claims abstract description 8
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 6
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 54
- -1 alkylaluminum halide Chemical class 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052782 aluminium Inorganic materials 0.000 claims description 22
- 239000003446 ligand Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001993 dienes Chemical class 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052744 lithium Inorganic materials 0.000 claims description 9
- 239000011777 magnesium Substances 0.000 claims description 9
- 229910052749 magnesium Inorganic materials 0.000 claims description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 8
- 229910052794 bromium Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052733 gallium Inorganic materials 0.000 claims description 6
- 150000008040 ionic compounds Chemical class 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 125000000962 organic group Chemical group 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 229910003002 lithium salt Inorganic materials 0.000 claims description 5
- 159000000002 lithium salts Chemical class 0.000 claims description 5
- 150000002902 organometallic compounds Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- IOWGHQGLUMEZKG-UHFFFAOYSA-N (2-bromophenyl)methanol Chemical compound OCC1=CC=CC=C1Br IOWGHQGLUMEZKG-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 238000006263 metalation reaction Methods 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 claims 6
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 241000682622 Andracantha sigma Species 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 150000002085 enols Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 27
- 238000007334 copolymerization reaction Methods 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 7
- 150000001450 anions Chemical class 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- 239000000243 solution Substances 0.000 description 50
- 229940093470 ethylene Drugs 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000306 component Substances 0.000 description 25
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 22
- 239000000178 monomer Substances 0.000 description 20
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 19
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 18
- AQZWEFBJYQSQEH-UHFFFAOYSA-N 2-methyloxaluminane Chemical compound C[Al]1CCCCO1 AQZWEFBJYQSQEH-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 230000001105 regulatory effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- VPGLGRNSAYHXPY-UHFFFAOYSA-L zirconium(2+);dichloride Chemical compound Cl[Zr]Cl VPGLGRNSAYHXPY-UHFFFAOYSA-L 0.000 description 8
- 229920002943 EPDM rubber Polymers 0.000 description 7
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- DKLQZDIAQKGVTA-UHFFFAOYSA-N 4,7-dimethyl-1h-indene Chemical compound CC1=CC=C(C)C2=C1CC=C2 DKLQZDIAQKGVTA-UHFFFAOYSA-N 0.000 description 6
- GCZQTQUHBZZQAC-UHFFFAOYSA-N 4,7-dimethyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=C(C)C2=C1CCC2=O GCZQTQUHBZZQAC-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 238000004073 vulcanization Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- FWYWKLULFJCQEB-UHFFFAOYSA-N 5,6-dimethyl-2,3-dihydro-1h-inden-1-ol Chemical compound C1=C(C)C(C)=CC2=C1C(O)CC2 FWYWKLULFJCQEB-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000012512 characterization method Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- ZAZMJPVXTZEDDN-UHFFFAOYSA-N 5,6-dimethyl-2,3-dihydroinden-1-one Chemical compound C1=C(C)C(C)=CC2=C1C(=O)CC2 ZAZMJPVXTZEDDN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229920000092 linear low density polyethylene Polymers 0.000 description 4
- 239000004707 linear low-density polyethylene Substances 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- ZCPRQJAMQLDMEB-UHFFFAOYSA-N 1-bromo-2-(2-methoxypropan-2-yloxymethyl)benzene Chemical compound COC(C)(C)OCC1=CC=CC=C1Br ZCPRQJAMQLDMEB-UHFFFAOYSA-N 0.000 description 3
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 3
- RDAOPSHEXLLEKN-UHFFFAOYSA-N 5,6-dimethyl-1h-indene Chemical compound C1=C(C)C(C)=CC2=C1C=CC2 RDAOPSHEXLLEKN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 235000013849 propane Nutrition 0.000 description 3
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 2
- RJUCIROUEDJQIB-GQCTYLIASA-N (6e)-octa-1,6-diene Chemical compound C\C=C\CCCC=C RJUCIROUEDJQIB-GQCTYLIASA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
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- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- GASOCDUVJSYZGK-UHFFFAOYSA-N spirobenzofuran Chemical class C1=2C=C(O)C(C)=CC=2OC(O)C21CC(=O)CC2(C)C GASOCDUVJSYZGK-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920001576 syndiotactic polymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 1
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
- C08F210/18—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers with non-conjugated dienes, e.g. EPT rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2420/00—Metallocene catalysts
- C08F2420/09—Cyclic bridge, i.e. Cp or analog where the bridging unit linking the two Cps or analogs is part of a cyclic group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65908—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an ionising compound other than alumoxane, e.g. (C6F5)4B-X+
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98MI000479A IT1298616B1 (it) | 1998-03-10 | 1998-03-10 | Complesso metallocenico pontato per la (co) polimerizzazione delle olefine |
| ITMI98/A000479 | 1998-03-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2262868A1 CA2262868A1 (en) | 1999-09-10 |
| CA2262868C true CA2262868C (en) | 2009-08-18 |
Family
ID=11379246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002262868A Expired - Fee Related CA2262868C (en) | 1998-03-10 | 1999-03-08 | Bridged metallocene complex for the (co)polymerization of olefins |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6211110B1 (enExample) |
| EP (1) | EP0955304B1 (enExample) |
| JP (1) | JP4372258B2 (enExample) |
| CN (1) | CN1198835C (enExample) |
| AT (1) | ATE248848T1 (enExample) |
| CA (1) | CA2262868C (enExample) |
| DE (1) | DE69910886T2 (enExample) |
| DK (1) | DK0955304T3 (enExample) |
| ES (1) | ES2207045T3 (enExample) |
| IT (1) | IT1298616B1 (enExample) |
| PT (1) | PT955304E (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1049704B1 (en) * | 1998-11-20 | 2005-07-27 | Basell Polyolefine GmbH | Bridged metallocenes, preparation, use in catalytic systems |
| ITMI20011017A1 (it) | 2001-05-17 | 2002-11-17 | Enichem Spa | Procedimento per la preparazione di copolimeri e terpolimeri elastomerici ep (d) m |
| US7060765B2 (en) | 2001-07-19 | 2006-06-13 | Univation Technologies, Llc | Low comonomer incorporating metallocene catalyst compounds |
| JP3928394B2 (ja) * | 2001-09-14 | 2007-06-13 | 住友化学株式会社 | 置換シクロペンタジエンおよびその製造方法 |
| US7439379B2 (en) | 2001-09-14 | 2008-10-21 | Sumitomo Chemical Co., Ltd. | Transition metal complex, catalyst for olefin polymerization, and process for producing olefin polymer with the same |
| ITMI20012516A1 (it) | 2001-11-30 | 2003-05-30 | Enichem Spa | Procedimento per la preparazione di copolimeri dell'etilene aventi una larga distribuzione dei pesi molecolari |
| US7541402B2 (en) | 2002-10-15 | 2009-06-02 | Exxonmobil Chemical Patents Inc. | Blend functionalized polyolefin adhesive |
| US7700707B2 (en) | 2002-10-15 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| US7550528B2 (en) * | 2002-10-15 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Functionalized olefin polymers |
| US7223822B2 (en) * | 2002-10-15 | 2007-05-29 | Exxonmobil Chemical Patents Inc. | Multiple catalyst and reactor system for olefin polymerization and polymers produced therefrom |
| WO2005108442A1 (en) | 2002-10-15 | 2005-11-17 | Exxonmobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| US20040102311A1 (en) * | 2002-11-21 | 2004-05-27 | Abbas Razavi | Bridged metallocene catalyst component, method of making, polyolefin catalyst having C1, C2, or Cs symmetry, methods of making, methods of polymerizing, olefins and products made thereof |
| JP5154748B2 (ja) * | 2005-10-21 | 2013-02-27 | 三井化学株式会社 | 連続有機過酸化物架橋ゴム成形体への加工法およびその架橋ゴム成形体 |
| JP2008231017A (ja) | 2007-03-20 | 2008-10-02 | Sumitomo Chemical Co Ltd | 遷移金属錯体、その製造方法及び用途 |
| KR100994252B1 (ko) | 2007-05-09 | 2010-11-12 | 주식회사 엘지화학 | 에틸렌 알파-올레핀 공중합체 |
| CN102149384B (zh) * | 2008-08-14 | 2014-08-20 | 南京奥昭生物科技有限公司 | 作为ep4受体拮抗剂的杂环酰胺衍生物 |
| US9000200B2 (en) * | 2011-12-19 | 2015-04-07 | Saudi Basic Industries Corporation | Process for the preparation of metallocene complexes |
| CN104093730A (zh) * | 2011-12-19 | 2014-10-08 | 沙特基础工业公司 | 用于制备茂金属络合物的方法 |
| JP6589233B2 (ja) * | 2015-03-17 | 2019-10-16 | 株式会社カネカ | トリアリールメタノールの製造方法 |
| EP3866927A4 (en) * | 2018-10-17 | 2022-07-27 | Nikang Therapeutics, Inc. | Indane derivatives as hypoxia inducible factor-2(alpha) inhibitors |
| CN109575300A (zh) * | 2018-11-15 | 2019-04-05 | 三明学院 | 一种导电金属有机框架材料的合成方法 |
| CN111793159B (zh) * | 2020-01-16 | 2021-04-06 | 深圳市沃尔电力技术有限公司 | 高压绝缘直流电缆附件材料生产方法及其加工设备 |
| US11613593B2 (en) | 2020-02-24 | 2023-03-28 | Exxonmobil Chemical Patents Inc. | Ansa-bis(inden-2-yl) catalysts for producing vinylidene-terminated polyalphaolefins |
| CN111620914B (zh) * | 2020-07-09 | 2021-03-19 | 吉林大学 | 含中性苄杂原子配位基侧臂单茂四价过渡金属配合物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1275777B1 (it) | 1995-07-06 | 1997-10-17 | Enichem Spa | Catalizzatore metallocenico per la (co)polimerizzazione delle olefine |
| US5635437A (en) * | 1995-07-28 | 1997-06-03 | Exxon Chemicals Patents, Inc. | Method for preparing metallocene catalyst systems |
| IT1282666B1 (it) | 1996-02-22 | 1998-03-31 | Enichem Spa | Catalizzatore metallocenico sostituito per la (co) polimerizzazione delle olefine |
| IT1283630B1 (it) | 1996-05-09 | 1998-04-23 | Enichem Spa | Procedimento per la preparazione di copolimeri elastomerici ep(d)m |
| IT1290856B1 (it) | 1996-12-19 | 1998-12-14 | Enichem Spa | Metalloceni, loro preparazione ed uso nella polimerizzazione di alfa-olefine |
| US6087515A (en) * | 1998-10-07 | 2000-07-11 | Solvay Polyolefins Europe-Belgium (Societe Anonyme) | Metallocenes and process for the preparation of metallocenes |
-
1998
- 1998-03-10 IT IT98MI000479A patent/IT1298616B1/it active IP Right Grant
-
1999
- 1999-02-26 AT AT99103742T patent/ATE248848T1/de active
- 1999-02-26 ES ES99103742T patent/ES2207045T3/es not_active Expired - Lifetime
- 1999-02-26 EP EP99103742A patent/EP0955304B1/en not_active Expired - Lifetime
- 1999-02-26 DK DK99103742T patent/DK0955304T3/da active
- 1999-02-26 PT PT99103742T patent/PT955304E/pt unknown
- 1999-02-26 DE DE69910886T patent/DE69910886T2/de not_active Expired - Lifetime
- 1999-03-04 US US09/262,318 patent/US6211110B1/en not_active Expired - Lifetime
- 1999-03-08 CA CA002262868A patent/CA2262868C/en not_active Expired - Fee Related
- 1999-03-10 JP JP06365399A patent/JP4372258B2/ja not_active Expired - Fee Related
- 1999-03-10 CN CNB991056426A patent/CN1198835C/zh not_active Expired - Lifetime
-
2001
- 2001-02-23 US US09/790,570 patent/US6417418B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20010031885A1 (en) | 2001-10-18 |
| JP4372258B2 (ja) | 2009-11-25 |
| US6417418B2 (en) | 2002-07-09 |
| ATE248848T1 (de) | 2003-09-15 |
| CN1198835C (zh) | 2005-04-27 |
| IT1298616B1 (it) | 2000-01-12 |
| JP2000038409A (ja) | 2000-02-08 |
| CN1239098A (zh) | 1999-12-22 |
| ITMI980479A1 (it) | 1999-09-10 |
| DE69910886T2 (de) | 2004-07-15 |
| EP0955304A2 (en) | 1999-11-10 |
| CA2262868A1 (en) | 1999-09-10 |
| US6211110B1 (en) | 2001-04-03 |
| EP0955304B1 (en) | 2003-09-03 |
| EP0955304A3 (en) | 2000-06-21 |
| DK0955304T3 (da) | 2004-01-05 |
| ES2207045T3 (es) | 2004-05-16 |
| DE69910886D1 (de) | 2003-10-09 |
| PT955304E (pt) | 2004-01-30 |
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Effective date: 20190308 |